


Sure as Hell

by theinsandoutsofcastiel



Category: Supernatural
Genre: Demon!Dean, F/M, Handcuffing, Multi, NSFW, Threesome, panty job
Language: English
Status: Completed
Published: 2016-02-06
Updated: 2016-02-06
Packaged: 2018-05-18 15:11:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,482
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5932867
Author URL: https://archiveofourown.org/users/theinsandoutsofcastiel/pseuds/theinsandoutsofcastiel
Summary: <blockquote class="userstuff">
              <p>Pairing is Demon!Dean x Reader x Crowley; Anyway, uh, here’s the basic storyline; Reader is a hunter, she knows Deanmon and Crowley, in fact she fancies the both of them and she goes to a bar after an exhausting Rugaru hunt. She’s playing pool, and winning often. Dean appears in the bar and distracts her, making her lose a game. They finally go outside & they get into a heated make out session and end up going back to Reader’s hotel room. She finds Crowley waiting for them on her bed. 3some happens. AND Hi, um, could you, um, maybe do a fic (Dean or Crowley or anyone really) with a panty job? *blushes* *runs and hides in the corner*</p>
            </blockquote>





	Sure as Hell

Warnings: Language, rough smut, panty job, handcuffing, oral, anal, threesome, multiple orgasms

Fic:

A smile spreads across your face as you sink the eight ball. “Sorry buddy,” you say, unapologetically, “Hand it over.” The man you had just beaten slaps a handful of cash against the pool table before storming off; sore loser. “Who’s up next?” you ask the audience you’d acquired. One of the guys pulls out his wallet and flashes you five one hundred dollar bills before grabbing a pool cue. You nod to him and wait for him to set up the game. You’d just got done with an exhausting Rugaru hunt and you needed a way to blow off steam. Winning a bunch of money seemed like a good way to go. Leaning on your pool cue, you let your gaze wander around the room and something catches your eye.

Dean Winchester sits at the bar without a care in the world. He tips his glass towards you and gives you a wink, making your cheeks heat up. You’d run into him, and his friend Crowley, on several occasions. At first, you’d been hunting them. The King of Hell and a Knight of Hell running around together was bad news. Despite that, they’d turned out to be more helpful than you’d expected. The more you ran into them, the more you started to like them. Now it was to the point where you had crushes on them both, not that you’d ever tell them that.

You turn back towards the pool table and get ready to take the first shot, pushing the thought of Dean from your mind. Money was on the line and you needed to concentrate. The first shot was perfect, the next less so. Dean moves into your line of vision, making you scratch. “Shit,” you whisper, your turn ending.

Dean distracts you each time you step up to take a shot, making your game awful. Before long, your opponent is close to winning. You have one last chance to catch up, but of course Dean distracts you again. He had started singing karaoke and even though you couldn’t see him, his awful singing was enough to draw your attention.

“God damnit,” you complain as your opponent sinks the eight ball.

“Cough it up Doll,” the man says, holding out his hand. You pull five hundred dollars out of your pocket and slap it into his hand, rolling your eyes at his smug look. Turning around, you run straight into Dean.

“What are you doing here?” you practically growl.

“I’m here to find you Sweetheart,” Dean tells you as you push past him, “Aren’t you happy to see me.”

“You just cost me five hundred dollars,” you say angrily, taking a seat at the bar, “No, technically you lost me a thousand. Now I’m even more pissed.”

“Oh come on,” Dean says, “I’m worth it.”

“What are you? A L’Oreal commercial?” you ask. Dean laughs as he leans down to whisper in your ear.

“Don’t order a drink. I need to talk to you, now,” Dean says, “Outside.”

“Fine, bossy,” you say grumpily as you slide off your seat. Dean follows you as you leave the bar and head around the side of the building.

The next thing you know, Dean has you pressed up against the wall, his lips on yours. His hands are all over your body, touching, grabbing, and groping. It surprises you at first, but it doesn’t take you long to react. You kiss him back, the two of you fighting for dominance. Your hands fist in his hair and in his jacket. One of Dean’s hands moves down to your thigh and pulls your leg up around his waist.

“I thought you said you wanted to talk,” you gasp as you try to catch your breath.

“This is better than talking though isn’t it?” he asks, grinding his hips against you.

“Fuck,” you hiss, his arousal evident.

“Exactly,” Dean growls, his lips right next to your ear, “That’s exactly what I want to do to you.”

“Not here,” you say, “Too public.”

“Your car?” Dean suggests.

“Unh-uh,” you respond, “I’ve got a motel room, not far from here.” Dean snaps his fingers and the next thing you know you’re in your motel room, you back pressed against the door. The room is dark save for the parking lot lights shining through the curtains. Dean doesn’t stop touching you, his hands all over your body.

“How did you know where I was staying?” you ask.

“Been watching you for a while now,” Dean explains between rough kisses, “We were waiting for the right time to do this.”

“We?” you question. Dean doesn’t answer, his lips capturing yours in a demanding kiss instead.

“Hello Darling,” a deep British voice says from somewhere behind Dean. You break the kiss with Dean and push him away just enough for you to see Crowley sitting on your bed, a fruity drink in his hand. He stands and snaps his fingers, turning on the lights before he starts moving towards you.

“What are you doing here?” you ask, afraid that this was some sort of trap; that they’d finally decided to get rid of you for good.

“Isn’t it obvious Love?” Crowley asks. He sets his drink down on the desk and snatches you away from Dean. The Winchester growls, but he lets Crowley pull you to him, your chest pressed against his. “This isn’t a trap, nor do we want to get rid of you,” Crowley assures, repeating the exact thoughts that had just run through your mind, “We know what you want from us.”

“What do you mean?” you question. You fist your hands into the lapels of Crowley’s suit jacket, your breathing shallow.

“We’ve heard all those dirty little thoughts in your head,” Dean tells you as he presses himself up against your back.

“You - you have?“ you stumble. Dean hums in confirmation as he kissed your neck.

"Oh Love, you have such dirty thoughts,” Crowley says, pushing a strand of hair behind your ear, “You’ve given us so many ideas.” You swallow hard and bite your bottom lip as Crowley’s hand comes up to cup your cheek, his thumb running over your lips.

“We know you want us,” Dean whispers in your ear, his hips rock against you, his hard cock prodding your ass cheek. You let your head fall back against his shoulder. He was right, you did want this. As they already knew, you’d had all kinds of dirty fantasies about them. You knew it was wrong. They were demons, the King and a Knight of Hell no less, and you were a hunter. You should want them dead, but you didn’t, you wanted something completely different.

Crowley’s kiss was much less demanding than Dean’s. It’s like he wanted to take his time and savor each moment. You let him take control of the kiss, his tongue slipping between your lips. He tasted just like that drink he had been drinking. His hands slide down your arms and find your hands before guiding them around his waist. You slide one hand up his back and fist both hands into his jacket, pulling him closer.

Dean’s hands find your hips, pulling you back against him as he grinds himself against your ass. Crowley’s make their way to the buttons of your flannel shirt. He opens each button agonizingly slowly, his fingers dancing along your skin as he reveals more and more of it. Dean’s hands slide to the front of your body, his fingers working open the front of your pants. You groan in frustration as you try in vain to remove Crowley’s clothing. He’s too busy with undressing you to let you undress him.

One of Dean’s hands slides into your pants, leaving your panties between his skin and yours. “She’s already soaked her panties,” Dean mutters against your neck as his fingers trace your slit through the material. Crowley smirks and laughs through his nose.

“Poor little hunter,” Crowley comments, “Brought so low by two demons. You want us don’t you?” Crowley’s hands press beneath the material of your jacket and shirt, the callused fingers sliding up and down your sides. One of his hands moves up to cup your breast through your bra, pinching the nipple through the material.

“Yes,” you whisper, your hips cantering towards Dean’s hand. You can feel him smirk against your skin.

“Sorry, what was that?” Crowley asks, “We couldn’t hear you.”

“Yes,” you say louder, tugging at Crowley’s clothes, “Please, I want you both.”

“That’s better,” Crowley praises. He snaps his fingers and makes his clothing disappear. His erect cock springs free and presses against your thigh. You gasp at the size of him, your fingertips digging into the skin of his back as you try to pull him closer. Crowley smirks at your efforts and thwarts them.

Dean pulls his hand from your pants as Crowley reaches for your hips. Working together, they spin you around, simultaneously pulling your shirt and jacket off. Dean’s hands reach for the clasp of your bra and open it before pulling the material from your body. Crowley pulls you back against him, now taking his turn to grind himself against your ass. Dean shrugs his jacket off and begins undressing himself before he thinks better of it. He snaps his fingers, removing all of your clothing save your panties. Snapping his fingers again, he removes his clothing, letting his hard cock free of its confines.

“Oh fuck,” you moan. They were both huge and so hard for you. You wanted them now and you weren’t above begging for it. “Please,” you say, reaching for Dean’s shoulders, “I need you both inside me. I need to feel you, please.”

“Now where’s the fun in that?” Dean asks, pressing himself up against you.

“We’re going to have a little fun with you first,” Crowley adds. Their hands and lips are all over your body, grasping and squeezing, kissing and sucking. You know they’re leaving marks on your body, but you don’t care.

You reach behind you with one hand, threading your fingers through Crowley’s hair. With your other hand, you drag your fingertips down Dean’s back. They tease you, touching you here and there, making you moan and whimper. You beg them both for more, but they enjoy teasing you too much. Crowley’s hand finds your panties and he pulls them away from your body, just enough to slip his cock beneath them. You moan and press your hips back against him, his cock sliding between your ass cheeks.

Dean mimics Crowley’s action, slipping his cock beneath your panties. He grinds himself against you, his hard cock sliding through your dripping folds. His tip presses against your clit over and over again, giving you the friction you’d been craving. You cling to them, rocking your hips back and forth in time with their motions. Their cocks slide against your skin, their tips leaking and making your panties even more wet. The grunts and groans leaving their lips make your stomach twist and coil.

They mumble strings of curses and your name under their breath, their cocks throbbing against you. “Gonna make us cum in your panties,” Dean tells you, his hips bucking against you. Crowley groans against your neck, sending vibrations through your skin.

“Fuck,” you whisper, your hands fisting in their hair. Crowley’s cock slides between your ass cheeks while Dean’s slides through your pussy lips over and over again, hitting your clit with each thrust.

“You feel so good,” Dean grunts. Their fingertips dig into your skin as they near their climaxes, their cocks twitching.

“I bet it’ll feel even better when we’re actually fucking you,” Crowley adds. You let your hand slip from Crowley’s hair and down his body until you reach his cock. Crowley groans as you stroke him, your panties between his cock and your hand. “Oh fuck,” Crowley grunts, his teeth finding your shoulder.

His cock pulses, his cum landing against your lower back and ass, soaking into your panties. The feeling combined with the feeling of Dean grinding himself against you sets off your orgasm. “Dean, Crowley,” you moan, your orgasm washing through you. You cling to them, holding them close as your body rocks between them.

“Shit,” Dean groans, “I’m gonna cum.” He pulls his cock from your panties and his fingers slip beneath the waistband, pulling them away from your body. “Fuck,” Dean whispers, his hand pumping over his length. Crowley pulls you back against him, kissing your neck and shoulders as Dean jerks himself off into your panties. “Shit, oh fuck,” Dean groans as his cock pulses in his hand, ribbon after ribbon of cum spilling against your skin and into your panties.

He lets the elastic snap back against your skin. The material of your panties soaks up his cum leaving a giant wet spot in them. “If your panties weren’t soaked before, they certainly are now,” Crowley chuckles.

“Damn you’re hot,” Dean mumbles, examining the mess they’d made out of you. He reaches for your panties and pushes them down. Removing them from your body, he balls them up and uses them to clean his cum from your body before handing them to Crowley.

“You can keep these as a souvenir,” Crowley says with a smirk as he wipes his cum from your back and ass. His hand presses against your back and he pushes you towards Dean. Dean grabs you and quickly leads you to the bed, pushing you down against it. He grabs your hands and pulls them up above your head, holding them there as he straddles your lap. The snap of Crowley’s fingers draws your attention. He stands beside the bed, a pair of handcuffs dangling over his index finger.

You lie back and let them cuff you to the bed. Dean moves to the side and lays down beside you, propping himself up on one elbow while his other hand traces random patterns up and down your body. Crowley spreads your legs wide and settles between them, his beard tickling your skin as he leaves kisses up and down your thighs. You squirm beneath Crowley’s touch as Dean captures your lips.

“We’re going to have so much fun with you Darling,” Crowley grumbles against your thigh. He kisses you here and there, making sure to avoid where you wanted him most.

You moan as Dean sucks one of your nipples between his lips, pulling the bud out between his teeth. His other hand grasps your neglected breast, kneading your flesh. Your back arches towards him, begging him for more. Crowley pulls one of your legs over his shoulder, the flat of his tongue pressing against your pussy lips. “I bet she tastes good, doesn’t she?” Dean asks.

Crowley hums against you, sending vibrations straight to your core. He buries his face between your legs, licking, sucking, and kissing. You pull at the restraints, wishing you could run your fingers through Crowley’s hair and pull him closer. Dean chuckles at your reaction and tells you to stay still or else they won’t give you what you want. You try desperately to stay still, but you can’t stop your hips from bucking towards Crowley, begging him for more as he teases you.

“It’s going to feel so good to be inside you,” Dean whispers in your ear, “Can’t wait to fuck you senseless.”

“Dean,” you moan, his words alone making your stomach twist. Apparently Crowley isn’t happy about your moaning. His teeth sink down into your thigh, making you gasp. Once he has your attention, he slides his tongue into you, exploring you lazily. “Crowley,” you moan, your body caving to his every touch.

“Such a dirty little hunter,” Dean whispers, “Just begging to be fucked by two demons.” You couldn’t stop your body from reacting to their touches, Dean kneading your breast, Crowley’s tongue swirling around inside you.

“Please,” you moan, coming closer and closer to climax. Crowley sucks your clit between his lips and slides two fingers into you, curling them against you as he pumps them in and out.

“We’re going to fulfill every last fantasy you’ve ever had,” Dean promises, “The only question is, how you want us to fuck you first?”

“Fuck,” you whisper, your walls fluttering around Crowley’s fingers.

“That’s right Baby Girl,” Dean says, “We’re gonna fuck you so hard.” Crowley slides a third finger into you and you lose it. You cry out as your orgasm crashes through you, your walls squeezing Crowley’s fingers. Your back arches from the bed as Crowley works you through your orgasm.

“You taste so sweet,” Crowley groans against you as he laps up everything you have to give him. He begins kissing his way up your body and pushes Dean away from you before he reaches for the handcuffs restraining you. Opening one, he unhooks you from the headboard and positions you on your knees with him behind you. He cuffs your hands behind your back and pushes you forward roughly, putting your lips right on level with Dean’s hard cock as he kneels before you. Crowley holds the chain between the handcuffs, keeping you level as he slides his cock between your slick folds.

Dean hooks a finger beneath your chin and brings your gaze to his, a smirk on his lips. “Are you gonna be a good girl for us?” Crowley asks, grinding his cock against your pussy lips.

“Yes,” you whisper.

“Gonna take our cocks so well aren’t you?” Dean asks. You swallow hard and nod your head in response. Dean takes his cock in his free hand and brings the tip to your lips, the salty precum leaking onto them. Without warning, Crowley thrusts into you hard, making you gasp. Dean takes the opportunity to press his tip between your lips. You swirl your tongue around his tip and suck lightly as Crowley sets a relentless pace.

Each of Crowley’s rough thrusts pushes you further onto Dean’s cock until his tip hits the back of your throat. You gag around him, but you don’t want him to stop. Dean groans as you hollow your cheeks, sucking him harder as you work the underside of his cock with your tongue. His hands twist into your hair and turn to fists as his head tips back, his lips parted in pleasure. Crowley’s free hand, grabs your hips, holding you still as he fucks you harder.

Dean’s hips thrust forward, fucking your throat. You hum around him, sending vibrations down his length. “Fuck,” he groans, “So fucking good.”

“You have no idea,” Crowley groans back. His cock slams into you again and again, bringing you closer and closer to your third orgasm. Crowley’s fingers slip from your hip and slide between your legs, quickly finding your clit. You moan as his fingers rub circles around your clit, the sensation making Dean’s thrusts fall out of rhythm.

“Oh fuck,” Dean groans his thrusts becoming more and more erratic. His hands tug your hair as he fucks your throat, his cock throbbing. Crowley’s thrusts are unrelenting, the combination of the two men fucking you like this making tears well in the corners of your eyes. “Oh shit,” Dean grunts, his cock pulsing and spilling cum down your throat, “Y/N!” His pulls himself from you as he comes down from his high, allowing you to catch your breath.

Crowley pulls the chain of the handcuffs, sitting you up on your knees. In one swift motion, he releases the chain and grasps your breast, squeezing the flesh as he pulls you back against him. His other hand continues rubbing your clit, making you whimper and moan as Crowley continues thrusting into you, faster than before. “Come around my cock Love,” Crowley demands, “Need to feel you cum.”

“Crowley,” you whimper, your walls growing tighter and tighter around him.

“That’s it Darling,” Crowley groans, “Make me cum.” One hard thrust combined with his fingers rubbing your clit sparks your orgasm.

“Crowley,” you call out as your walls come crashing down around his cock.

“Y/N!” Crowley grunts, his cock pulsing as your orgasm sparks his. You rest your head back against his shoulder, letting your body melt against his.

“Fuck, that was amazing,” you whisper.

“You don’t honestly think we’re done with you yet, do you?” Dean asks. Crowley pulls himself from you and Dean pulls you towards him before throwing you down against the bed. You bounce on the bed as your back hits the sheets. Sitting on his knees beside you, Dean hand grabs your thighs and spread your legs wide as Crowley thrusts two fingers deep into you.

Swirling his fingers inside you, he scoops up as much of his cum as he can before pulling his fingers from you. “I have to get you ready for me,” Crowley explains, his fingers pressing against your tight ass hole. He uses his cum as lube, slipping the two fingers into your back entrance. You moan as he stretches you out, getting you ready for him.

“Next time it’ll be my name you’re screaming,” Dean says, pushing three fingers into your already sensitive pussy. You buck your hips towards their hands, riding their fingers. “Crowley’s good, but I’m better,” he adds.

“In your dreams Winchester,” Crowley retorts, “I will always be a better lover than you; and soon, our little hunter here will be able to attest to it.”

“Yeah right,” Dean scoffs, “We’ll see about that.” This was quickly turning into a competition and you were all too happy to be in the middle of it. “I’m gonna feel so good inside you Baby,” Dean promises as he curls his fingers inside you.

“But not as good as me,” Crowley argues. He slides a third finger into you, stretching you further. You can’t help but writhe on the bed. They smirk as they watch your over sensitive body cave to their every touch.

“You’re going to cum again aren’t you?” Dean asks knowingly. His fingers curl against your g-spot, making your back arch from the bed.

“Cum for us one more time,” Crowley urges, “Then we can give you what you really want.”

“You know you want it,” Dean says, “Crowley fucking your ass, me fucking your tight little pussy.”

“Don’t try to deny it,” Crowley adds, “We’ve seen it in that dirty little mind of yours.”

“Please,” you moan.

“That’s a good girl,” Dean praises, “All you have to do is cum for us.” You rock your hips faster, desperate to make yourself cum.

“I want you both inside me,” you tell them, moaning as you ride their fingers.

“Don’t tell us Love,” Crowley says, “Show us.”

“That’s it,” Dean praises, your walls growing tight, “Cum around our fingers, then we’ll let you cum around our cocks.”

“Fuck,” you moan, “Crowley, Dean.” You wanted them, badly. The thought of having their cocks filling you to the brim sends you over the edge. You cry out their names as you reach your climax, your body turning to putty. Your walls clamp down around their fingers as your orgasm washes over you. You should be thoroughly exhausted, but you wanted more.

They give you hardly any time to recover before they reposition you. Crowley kneels behind you, Dean in front. Dean holds your hips, keeping you still as Crowley slicks his cock in your juices. Without wasting any more time, Crowley positions the tip of his cock at your back entrance and pushes in slowly. The burn you feel quickly gives way to pleasure as you push your hips back towards him, taking him all the way in.

Dean follows quickly, sliding his cock into your dripping pussy. You felt so full, having them both inside you like this. The feeling was intoxicating. They start thrusting in time with each other, creating a rhythm between the three of you that sends you reeling. You melt between them, your head falling forward against Dean’s shoulder.

“I want you to touch me,” Dean groans, brushing your hair over your shoulder. He snaps his fingers and the handcuffs disappear. Your hands are on them in an instant. You card your hands through their hair, drag your nails down their backs, sink your fingertips into their shoulders, grab their asses and pull them deep into you. Their hands explore your body as yours explore theirs’. They kiss your neck and nip at the skin of your shoulders.

They mark your body with their lips and hands, leaving evidence of the fucking they were giving you. “Dean! Crowley!” you cry out as you ride their cocks. You knew you couldn’t hold on much longer. Your body was already so sensitive from your four previous orgasms.

“Don’t cum yet,” Crowley commands, “I know you’re close, but you have to wait.” You fist your hands in their hair as your stomach knots.

“Please,” you whimper, “I’m so close, I can’t hold on any longer.”

“I know Baby Girl,” Dean groans, “Just a little longer ok?” You shut your eyes and try to concentrate, holding on for as long as you could while they fucked you senseless.

“Y/N,” Crowley groans, “Fuck you’re tight. Y/N, fuck!” Crowley’s hands hold you tightly as his cock pulses, spilling his cum deep inside you. The feeling is too much.

“Crowley! Dean!” you shout, screaming their names as your orgasm hits you hard, your walls clamping down around their cocks. Dean’s orgasm follows yours, his cock pulsing as his cum splashes against your walls. He grunts your name and a string of curses as his hips buck against you. Their orgasms prolong yours and vice versa, helping each other ride out your highs until your body collapses between them. Dean catches you, laughing at your blissful expression.

“I think our little hunter needs some rest,” Crowley chuckles.

“Well deserved I’d say,” Dean says, running his hand through your hair.

They pull themselves from you and let you lie back against the pillows, one of them lying to either side of you. “That was … wow,” you laugh, unable to put it in words.

“Trust us, we know,” Dean says, “By the way, in the spirit of friendly competition, which of us was better?”

“I’m still deciding,” you say sleepily, yawning as you settle in beneath the sheets.

“Don’t worry Love, get some rest,” Crowley tells you, “There will be plenty of time for you to decide; and plenty of chances for us to compete.”

“There will be?” you ask a little surprised. If they wanted you, you weren’t going to complain, but you hadn’t expected the demons to want to stick around.

“Sure,” Dean says, “This isn’t a one and done type of thing. We sure as Hell aren’t done with you yet.”


End file.
